US2804455A - Monoazo dyestuffs and their metal complex compounds - Google Patents
Monoazo dyestuffs and their metal complex compounds Download PDFInfo
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- US2804455A US2804455A US505838A US50583855A US2804455A US 2804455 A US2804455 A US 2804455A US 505838 A US505838 A US 505838A US 50583855 A US50583855 A US 50583855A US 2804455 A US2804455 A US 2804455A
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- parts
- monoazo
- hydroxy
- dyestuffs
- complex compounds
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- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 title claims description 23
- -1 metal complex compounds Chemical class 0.000 title description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 14
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- 229910052804 chromium Inorganic materials 0.000 description 9
- 239000011651 chromium Substances 0.000 description 9
- 239000000975 dye Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 8
- 238000000034 method Methods 0.000 description 7
- 210000002268 wool Anatomy 0.000 description 7
- 150000008049 diazo compounds Chemical class 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 235000011121 sodium hydroxide Nutrition 0.000 description 5
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 4
- 238000010168 coupling process Methods 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000002843 carboxylic acid group Chemical group 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000008878 coupling Effects 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 125000000542 sulfonic acid group Chemical group 0.000 description 3
- VLZVIIYRNMWPSN-UHFFFAOYSA-N 2-Amino-4-nitrophenol Chemical compound NC1=CC([N+]([O-])=O)=CC=C1O VLZVIIYRNMWPSN-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 150000004996 alkyl benzenes Chemical class 0.000 description 2
- 150000001555 benzenes Chemical class 0.000 description 2
- 238000004043 dyeing Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 229940124530 sulfonamide Drugs 0.000 description 2
- HINGJEDHCQTIOB-UHFFFAOYSA-N 1-(2-hydroxy-5-methylphenyl)pyrrolidin-2-one Chemical compound OC1=C(C=C(C=C1)C)N1C(CCC1)=O HINGJEDHCQTIOB-UHFFFAOYSA-N 0.000 description 1
- AACMNEWXGKOJJK-UHFFFAOYSA-N 2-amino-6-nitrophenol Chemical compound NC1=CC=CC([N+]([O-])=O)=C1O AACMNEWXGKOJJK-UHFFFAOYSA-N 0.000 description 1
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- PYKNDCILXQWMJP-UHFFFAOYSA-N azane;chromium(3+) Chemical compound N.[Cr+3] PYKNDCILXQWMJP-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
- 235000021240 caseins Nutrition 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Substances ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Substances [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000004929 pyrrolidonyl group Chemical group N1(C(CCC1)=O)* 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- KIEOKOFEPABQKJ-UHFFFAOYSA-N sodium dichromate Chemical compound [Na+].[Na+].[O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O KIEOKOFEPABQKJ-UHFFFAOYSA-N 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B45/00—Complex metal compounds of azo dyes
- C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
- C09B45/14—Monoazo compounds
Definitions
- the present invention relates to monoazo dyestuffs, their metal complex compounds and to methods of making the same; more particularly it relates to monoazo dyestuffs corresponding to the following formula:
- the invention further relates to metal complex compounds of these mo'n'oaZo dyestuffs.
- the new monoazo dyestufis can be obtained by coupling the diazo compounds of o-hydroxy aminobenzenes with components of the following. formula:
- the monoazo dystuffs thus obtained can be converted into their metal complex compounds by a treatment with metal yielding agents in usual manner either on the fibre or in the dye bath or in substance.
- the dyestuffs are e. g. well suited for the monochrome process.
- the conversion of the new dyestutfs in their metal complex compounds, preferably into their chromium complex compounds, may be carried out in admixture with other metallizable monoazo dyestuffs.
- metal containing d'yestuifs in substance takes place in the usual manner, e. g. in the absence or presence of complex forming compounds such as oxalic acid, salicylic acid, etc.
- Suitable diazo compounds for the production of the new dyestuffs are e. g. l-amino-2-hydroxy-5-chlorobenzene, 1-amino-2'-hydroxy-3,5-dichlorobenzene, 1-amino-2- hydroxy--nitrobenzene, 1 amino-2-"hydroxy-3-chloro-5- nitrobenzene, 1 amino-Z-hydroxy-3-nitrobenzene-S-sulfonamide, 1 amino-2-hydroXy-3-nitrobenZene-S-methylsulfone, etc.
- the 1 hydroxy 2 [pyrrolidonyl( l")"]-4 alkylbenzenes used as coupling components inthe present process may contain straight-chained, branched or cyclic alkyl groups with 1 to 8 carbon atomsr They are obtained by the reaction of 1-hydroxy-2-amino-4 alkylbenzenes with 'ybutyrolactone, as described in Berichte der Deutschen Chemischen Gesellschaf 69, page 2727.
- the coupling process is carried out in water or organic ice solvents as dimethyl torrnamide, in the presence of acid binding materials as soda lye, ammonia, soda, milkof lime, magnesium carbonate or pyridine.
- the new monoazo dyestuffs yield on wool, afterchromed, brownish-red to brown dyeings of very good fastness to light and good fastness to wear and tear and good fastness to processing.
- the dyestuffs metallized in substance dye wool and silk as well as wool-like synthetic fibres from superpolyamides, superpolyurethanes and casein fibres as well as leather from neutral or weakly acid bath; they possess excellent leveling and penetrating properties. In these properties they exceed other comparable known dyestuifs, which contain instead of the pyrrolidine group e. g. a'n acetylarnino group.
- the dyeings thus obtained possess a very good fastness to light and good fastness to wear and tear and to processing.
- the new monoazo dyestuffs which are chromed in admixture with other monoazo dyestufis show similar general and fastness properties.
- Example 1 15.4 parts of 1-amino-2-hydroxy-5-nitrobenzene are indirectly diazotized in usual manner and the formed diazo compound salted out and filtered with suction.
- the separated diazo compound is gradually added with stirring to a solution of 192 parts of 1-hydroxy-2-(N-pyrroli donyl)-4-methylbenzene, 4 parts of sodium hydroxide in 350 parts of pyridine and 40 parts of water which is cooled to a temperature of -10 C. to -5 C.
- the pyridine is distilled oil in vacuo and the formed monoazo dyestufl corresponding to the following general formula:
- N02 CH2 is purified by dissolving it in water and salting out.
- a black powder is obtained which dyes wool by the monochrome process in reddish-brown shades.
- Example 2 35.6 parts of the monoazo dyestutf, described in Example 1, are dissolved in 350 parts of hot water and 40 parts of 10 per cent soda solution. 200 parts of an chromium-ammonium-'oxalate solution which corresponds to 26 parts of chrome per litre, are d'ropwise added to the solution of the monoazo dyestuif with stirring at a temperature of -100 C. When the reaction is finished the chrome containingmonoazo dyestufi is filtered with suction and dried. It represents a black powder which dyes wool from a neutral or weakly acid bath in reddishbrown shades of good fastness properties.
- a chromium complex dyestuif of similar properties is obtained, if a solution of 7.9 parts of sodium bichromate and 6 parts of 40 percent sodium hydroxide in 30 parts of water together with asolution of 10 parts of commercial glucose in- 40 parts of water is added dropwise with stirring. to a solution of 35:6 partsof the aforesaid dyestutf in 250 parts of water and 12 parts of- 40 percent sodium hydroxide at a temperature of 95 C.
- Example 3 23.3 parts of l-amino-2-hydroxy-3-nitrobenzene-5-sulfonamide are diazotized with 6.9 parts of sodium nitrite in usual manner and combined with 19.2 parts of 1- hydroxy 2 (N-pyrrolidonyl)-4-methylbenzene as described in Example 1. After distilling off the pyridine the dyestuif is redissolved from water. A monoazo dyestulf of the following formula is obtained:
- Example 4 15.4 parts of 1-amino-2-hydroxy-5-nitrobenzene are diazotized as described in Example 1.
- the separated diazo compound is added to a solution of 23.3 parts of 1-hydroxy-2-(N-pyrrolidonyl)-4-tertiary-butyl-benzene, 4 parts of sodium hydroxide and 8 parts of soda in 350 parts of pyridine and 50 parts of Water.
- the further process is the same as described in Example 1.
- the dyeand forms, after drying, a dark powder which dyes wool by the monochrome process in dark red-brown shades of excellent fastness properties.
- the l hydroxy 2-(N-pyrrolidonyl)-4-tertiary-butylbenzene can be obtained by reacting l-hydroxy-Z-amino- 4-tertiary-butyl-benzene with 'y-butyrolactone at a temperature of about 250 C. It forms colorless needles melting at 151 C.
- a dyestuff selected from the group consisting of a monoazo dyestutf corresponding to the formula i C CH2 and the chromium ICOITIPIEZX compound thereof.
- a dyestutf selected from the group consisting of the monoazo dyestuif corresponding to the formula:
- a dyestulf selected from the group consisting of a monoazo dyestuff corresponding to the formula and the chromium complex compound thereof.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
United States Patent MONOAZO DYESTUFFS AND THEIR METAL COMPLEX COMPOUNDS Alfons Dorlars, Leverkusen-Schlebusch, and Otto Bayer and Edgar Enders, Leverkusen-Bayerwerk, Germany, assignors to. Farbenfabrikeri Bayer Aktier'l'ges'ellschatt, Leverkusen, Germany, a corporation of Germany No Drawing. Application May 3, 1955,
Serial N0. 505,838
Claims priority, application Germany May 8, 1954 7 Claims. (CL 260-446) The present invention relates to monoazo dyestuffs, their metal complex compounds and to methods of making the same; more particularly it relates to monoazo dyestuffs corresponding to the following formula:
in this formula R stands for a radical of the benezene series being free from sulfonic and carboxylic acid groups and bearing the hydroxy group in o-position to the -N=N-bridge. The invention further relates to metal complex compounds of these mo'n'oaZo dyestuffs.
The new monoazo dyestufis can be obtained by coupling the diazo compounds of o-hydroxy aminobenzenes with components of the following. formula:
o oorn which couple in o-position to the hydroxy group.
The monoazo dystuffs thus obtained can be converted into their metal complex compounds by a treatment with metal yielding agents in usual manner either on the fibre or in the dye bath or in substance. The dyestuffs are e. g. well suited for the monochrome process.
The conversion of the new dyestutfs in their metal complex compounds, preferably into their chromium complex compounds, may be carried out in admixture with other metallizable monoazo dyestuffs.
The manufacture of metal containing d'yestuifs in substance takes place in the usual manner, e. g. in the absence or presence of complex forming compounds such as oxalic acid, salicylic acid, etc.
Suitable diazo compounds for the production of the new dyestuffs are e. g. l-amino-2-hydroxy-5-chlorobenzene, 1-amino-2'-hydroxy-3,5-dichlorobenzene, 1-amino-2- hydroxy--nitrobenzene, 1 amino-2-"hydroxy-3-chloro-5- nitrobenzene, 1 amino-Z-hydroxy-3-nitrobenzene-S-sulfonamide, 1 amino-2-hydroXy-3-nitrobenZene-S-methylsulfone, etc.
The 1 hydroxy 2 [pyrrolidonyl( l")"]-4 alkylbenzenes, used as coupling components inthe present process may contain straight-chained, branched or cyclic alkyl groups with 1 to 8 carbon atomsr They are obtained by the reaction of 1-hydroxy-2-amino-4 alkylbenzenes with 'ybutyrolactone, as described in Berichte der Deutschen Chemischen Gesellschaf 69, page 2727.
The coupling process is carried out in water or organic ice solvents as dimethyl torrnamide, in the presence of acid binding materials as soda lye, ammonia, soda, milkof lime, magnesium carbonate or pyridine.
The new monoazo dyestuffs yield on wool, afterchromed, brownish-red to brown dyeings of very good fastness to light and good fastness to wear and tear and good fastness to processing.
The dyestuffs metallized in substance dye wool and silk as well as wool-like synthetic fibres from superpolyamides, superpolyurethanes and casein fibres as well as leather from neutral or weakly acid bath; they possess excellent leveling and penetrating properties. In these properties they exceed other comparable known dyestuifs, which contain instead of the pyrrolidine group e. g. a'n acetylarnino group. The dyeings thus obtained possess a very good fastness to light and good fastness to wear and tear and to processing.
The new monoazo dyestuffs which are chromed in admixture with other monoazo dyestufis show similar general and fastness properties.
The following examples illustrate the invention, without, however, limiting it thereto; the parts being by weight:
Example 1 15.4 parts of 1-amino-2-hydroxy-5-nitrobenzene are indirectly diazotized in usual manner and the formed diazo compound salted out and filtered with suction. The separated diazo compound is gradually added with stirring to a solution of 192 parts of 1-hydroxy-2-(N-pyrroli donyl)-4-methylbenzene, 4 parts of sodium hydroxide in 350 parts of pyridine and 40 parts of water which is cooled to a temperature of -10 C. to -5 C. After coupling is finished the pyridine is distilled oil in vacuo and the formed monoazo dyestufl corresponding to the following general formula:
0 OH HO /C-CH2 N=N N\ l CHrCH:
N02 CH2 is purified by dissolving it in water and salting out. A black powder is obtained which dyes wool by the monochrome process in reddish-brown shades.
Example 2 35.6 parts of the monoazo dyestutf, described in Example 1, are dissolved in 350 parts of hot water and 40 parts of 10 per cent soda solution. 200 parts of an chromium-ammonium-'oxalate solution which corresponds to 26 parts of chrome per litre, are d'ropwise added to the solution of the monoazo dyestuif with stirring at a temperature of -100 C. When the reaction is finished the chrome containingmonoazo dyestufi is filtered with suction and dried. It represents a black powder which dyes wool from a neutral or weakly acid bath in reddishbrown shades of good fastness properties.
A chromium complex dyestuif of similar properties is obtained, if a solution of 7.9 parts of sodium bichromate and 6 parts of 40 percent sodium hydroxide in 30 parts of water together with asolution of 10 parts of commercial glucose in- 40 parts of water is added dropwise with stirring. to a solution of 35:6 partsof the aforesaid dyestutf in 250 parts of water and 12 parts of- 40 percent sodium hydroxide at a temperature of 95 C.
Example 3 23.3 parts of l-amino-2-hydroxy-3-nitrobenzene-5-sulfonamide are diazotized with 6.9 parts of sodium nitrite in usual manner and combined with 19.2 parts of 1- hydroxy 2 (N-pyrrolidonyl)-4-methylbenzene as described in Example 1. After distilling off the pyridine the dyestuif is redissolved from water. A monoazo dyestulf of the following formula is obtained:
It represents a black-brown powder which dyes wool by the monochrome process in reddish dark-brown shades of good fastness to light and good fastness to wet-treatment.
Example 4 15.4 parts of 1-amino-2-hydroxy-5-nitrobenzene are diazotized as described in Example 1. The separated diazo compound is added to a solution of 23.3 parts of 1-hydroxy-2-(N-pyrrolidonyl)-4-tertiary-butyl-benzene, 4 parts of sodium hydroxide and 8 parts of soda in 350 parts of pyridine and 50 parts of Water. The further process is the same as described in Example 1. The dyeand forms, after drying, a dark powder which dyes wool by the monochrome process in dark red-brown shades of excellent fastness properties.
If the dyestuif is chromed as described in Example 2, a chrome complex monoazo dyestuif is obtained which dyes wool from a neutral bath in level red-brown shades of good fastness to light and very good fastness to wettreatment.
The l hydroxy 2-(N-pyrrolidonyl)-4-tertiary-butylbenzene can be obtained by reacting l-hydroxy-Z-amino- 4-tertiary-butyl-benzene with 'y-butyrolactone at a temperature of about 250 C. It forms colorless needles melting at 151 C.
We claim:
1. Dyestuffs selected from the group consisting of monoazo dyestuffs corresponding to the general formula wherein R stands for a radical of the benzene series being free from sulfonic and carboxylic acid groups and bearing the hydroxy group in o-position to the N=N-bridge and R1 is an alkyl group having 1-8 carbon atoms and the chromium complex compounds thereof.
2. Dyestuffs selected from the group consisting of monoazo dyestuffs corresponding to the general formula wherein R stands for a radical of the benzene series being free from sulfonic and carboxylic acid groups and hearing the hydroxy group in o-position to the --N=N-bridge and the chromium complex compounds thereof.
3. A dyestuff selected from the group consisting of a monoazo dyestutf corresponding to the formula i C CH2 and the chromium ICOITIPIEZX compound thereof.
4. A dyestutf selected from the group consisting of the monoazo dyestuif corresponding to the formula:
OH HO I /CCH2 02N- N N CHz-OHz SOzNH7 H3 and the chromium complex thereof.
5. A dyestutf selected from the group consisting of a monoazo dyestuif corresponding to the formula OH HO /CCH2 Cl- N=N N I CHPCHQ CHa and the chromium complex compound thereof.
6. A dyestulf selected from the group consisting of a monoazo dyestuff corresponding to the formula and the chromium complex compound thereof.
7. A dyestufi selected from the group consisting of a monoazo dyestutf corresponding to the formula 0 OH HO ([L CH2 Ol- N=N N\ I CH2CH N02 CH:
and the chromium complex compound thereof.
[No references cited.
Claims (1)
1. DYESTUFFS SELECTED FROM THE GROUP CONSISTING OF MONOAZO DYESTUFFS CORRESPONDING TO THE GENERAL FORMULA
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2804455X | 1954-05-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2804455A true US2804455A (en) | 1957-08-27 |
Family
ID=7998720
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US505838A Expired - Lifetime US2804455A (en) | 1954-05-08 | 1955-05-03 | Monoazo dyestuffs and their metal complex compounds |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2804455A (en) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2873267A (en) * | 1956-07-20 | 1959-02-10 | Sandoz Ag | Monoazo dyestuffs and their metal complex compounds |
| US2933365A (en) * | 1957-11-20 | 1960-04-19 | Joseph E Moore | Dyeing and chemical modification of keratins |
| US3088837A (en) * | 1959-09-23 | 1963-05-07 | Gen Aniline & Film Corp | Preparation of paint compositions containing a pyrrolidone compound |
| US3386987A (en) * | 1965-10-08 | 1968-06-04 | Eastman Kodak Co | Azo dyes for containing dicarboximido groups |
| US3462408A (en) * | 1965-02-05 | 1969-08-19 | Bayer Ag | Monoazo dyestuffs containing a 6-hydroxynaphthostyrile group |
| US3666746A (en) * | 1969-06-25 | 1972-05-30 | Gaf Corp | Pyrrolidonylphenyl azo dyestuffs |
| US3943120A (en) * | 1967-09-19 | 1976-03-09 | Ciba-Geigy Ag | Succinimido azo dyestuffs |
| US5230241A (en) * | 1990-12-27 | 1993-07-27 | S.A. Andre Boet | Ground testing installation for an aircraft jet engine having a steerable nozzle |
-
1955
- 1955-05-03 US US505838A patent/US2804455A/en not_active Expired - Lifetime
Non-Patent Citations (1)
| Title |
|---|
| None * |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2873267A (en) * | 1956-07-20 | 1959-02-10 | Sandoz Ag | Monoazo dyestuffs and their metal complex compounds |
| US2933365A (en) * | 1957-11-20 | 1960-04-19 | Joseph E Moore | Dyeing and chemical modification of keratins |
| US3088837A (en) * | 1959-09-23 | 1963-05-07 | Gen Aniline & Film Corp | Preparation of paint compositions containing a pyrrolidone compound |
| US3462408A (en) * | 1965-02-05 | 1969-08-19 | Bayer Ag | Monoazo dyestuffs containing a 6-hydroxynaphthostyrile group |
| US3386987A (en) * | 1965-10-08 | 1968-06-04 | Eastman Kodak Co | Azo dyes for containing dicarboximido groups |
| US3943120A (en) * | 1967-09-19 | 1976-03-09 | Ciba-Geigy Ag | Succinimido azo dyestuffs |
| US3666746A (en) * | 1969-06-25 | 1972-05-30 | Gaf Corp | Pyrrolidonylphenyl azo dyestuffs |
| US5230241A (en) * | 1990-12-27 | 1993-07-27 | S.A. Andre Boet | Ground testing installation for an aircraft jet engine having a steerable nozzle |
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